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Best results for

Sailing

Showing 337-360 of 1,008 results
Key West, FL86Honolulu, HI65San Diego, CA35St. Augustine, FL28Traverse City, MI26
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  • New York, NY24
  • Charleston, SC21
  • Chicago, IL18
  • Hilton Head Island, SC17
  • Boston, MA16
  • Newport, RI15
  • Saint Michaels, MD15
  • Pensacola Beach, FL14
  • Bluffton, SC13
  • Cocoa Beach, FL12
  • Salem, MA12
  • Destin, FL11
  • Marina del Rey, CA11
  • San Francisco, CA11
  • Irvington, VA10
  • Kennebunkport, ME10
  • Manteo, NC10
  • Oceanside, CA10
  • Boothbay Harbor, ME9
  • Camden, ME9
Dolphin & Monkey Sailing Cruise on Saint Helena Island

Dolphin & Monkey Sailing Cruise on Saint Helena Island

Sail quiet Lowcountry waterways while looking for dolphins and Morgan Island monkeys

5.0 • 39 reviews
$371
3.5-Hour Sailing Lesson in Saint Helena Island

3.5-Hour Sailing Lesson in Saint Helena Island

Take the helm with a private, customizable keelboat sailing lesson

5.0 • 39 reviews
$477
Sailing & Snorkeling on a 6.5-Hour Cozumel Cruise

Sailing & Snorkeling on a 6.5-Hour Cozumel Cruise

Sail to Cozumel's northern beaches with snorkeling, lunch and drinks

4.9 • 72 reviews
$127/ person
Cozumel Sunset Sail

Cozumel Sunset Sail

Ease into sunset with drinks, music, and snacks on the water

4.9 • 72 reviews
$48/ person
Cozumel Northern Beaches Sailing Cruise

Cozumel Northern Beaches Sailing Cruise

Snorkel, dine, and sail Cozumel’s northern coast aboard the Tucan trimaran

4.9 • 72 reviews
$106/ person
Learn To Sail On A Hobie Catamaran

Learn To Sail On A Hobie Catamaran

Sail with an instructor for an easy, first-time-friendly session on calm Soundside waters

4.9 • 71 reviews
$106/ person
Performance Keelboat Sailing in Wrightsville Beach

Performance Keelboat Sailing in Wrightsville Beach

Race-boat sailing with a certified captain near Wrightsville Beach

4.9 • 71 reviews
$95/ person
2-Day Learn to Sail Class in Wrightsville Beach

2-Day Learn to Sail Class in Wrightsville Beach

Learn basic sailing in two after-work classes at Soundside

4.9 • 71 reviews
$313/ person
Sunset Sailing Cruise in Key West With Live Music

Sunset Sailing Cruise in Key West With Live Music

Sip and sail into the Key West sunset with live music and an open well bar

4.8 • 24.1K reviews
$60/ person
Sunset Sail in Aruba

Sunset Sail in Aruba

Sail into Aruba's sunset with tropical treats and an open bar

4.8 • 26.6K reviews
$136/ person
3-Hour Private Catamaran Cruise in Aruba

3-Hour Private Catamaran Cruise in Aruba

Private sailing with premium drinks, curated bites, and snorkeling

4.8 • 26.6K reviews
$2,373& up
Private Aruba Sunset Catamaran Cruise

Private Aruba Sunset Catamaran Cruise

Set sail on a private catamaran as Aruba’s coastline glows at sunset

4.8 • 26.6K reviews
$2,034& up
Private Catamaran Sail in Aruba

Private Catamaran Sail in Aruba

Sail privately in Aruba with snorkeling, curated bites and premium beverages

4.8 • 26.6K reviews
$2,486& up
Hilton Head Sailing on Historic America's Cup Yacht

Hilton Head Sailing on Historic America's Cup Yacht

Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

4.8 • 8.1K reviews
$55/ person
Sunset Cruise in Waikiki

Sunset Cruise in Waikiki

Sail the Waikiki coastline as day turns to night

4.8 • 5.5K reviews
$65/ person
America's Cup Sailing Cruise in Hilton Head

America's Cup Sailing Cruise in Hilton Head

Sail Hilton Head’s coast aboard the historic Stars & Stripes

4.8 • 8.1K reviews
$1,445
Hilton Head Island Sunset Sailing Cruise

Hilton Head Island Sunset Sailing Cruise

Sail the historic Stars & Stripes into a Hilton Head sunset

4.8 • 8.1K reviews
$1,766
Honolulu Sunset Sailing Cruise

Honolulu Sunset Sailing Cruise

Sail into sunset views with a relaxed evening on the water

4.8 • 2.4K reviews
$98/ person
Catamaran Sail in Honolulu with Diamond Head Views

Catamaran Sail in Honolulu with Diamond Head Views

Sail past Waikiki and Diamond Head with a full bar onboard

4.8 • 2.4K reviews
$98/ person
Waikiki Friday Fireworks Cruise

Waikiki Friday Fireworks Cruise

Sail at sunset for Waikiki Beach fireworks views

4.8 • 1.6K reviews
$87/ person
Aruba Sunset Sail

Aruba Sunset Sail

Sail Aruba's coast as day turns to night

4.8 • 1.6K reviews
$66/ person
54' Catamaran Sunset Sail in St. Thomas

54' Catamaran Sunset Sail in St. Thomas

Ease into the evening with appetizers and an open-air sunset sail

4.8 • 1.2K reviews
$91/ person
Private Catamaran Snorkel Trip to Icacos Island from Fajardo

Private Catamaran Snorkel Trip to Icacos Island from Fajardo

Private sailing day with lunch, drinks, and snorkeling gear

4.8 • 901 reviews
$10,909/ boat
Icacos Sunset Sailing Cruise From Fajardo

Icacos Sunset Sailing Cruise From Fajardo

Beach time at Icacos Cay followed by a Caribbean twilight cruise

4.8 • 901 reviews
$121/ person
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